Cannabidiol dimethyl ether

- Overview
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    Background
    
    Cannabidiol dimethyl ether (CBDD) is a cannabidiol derivative that potently and selectively inhibits 15-LOX with an IC50 value of 0.28 μM. 15-LOX can oxygenate cholesterol esters in the low-density lipoprotein (LDL) particle. Thus, 15-LOX has been involved in the development of atherosclerosis, and CBDD may be a useful prototype for producing medicines for atherosclerosis [1]. CBDD showed a potent inhibitory effect on the catalytic activity of cytochrome P450 2C19 with an IC50 value of 14.8 μΜ [2]. CBDD inhibited the CYP2B6 activity with the IC50values of 75.7 μM [3]. Cytochrome P450 enzymes have been isolated from numerous mammalian tissues such as liver, kidney, lung, intestine, adrenal cortex. Cytochrome P450 enzymes have also existed in insects, plants, yeasts, and bacteria. Cytochrome P450 has been known to catalyze hydroxylations, epoxidations, N-, S-, and O-dealkylations, N-oxidations, sulfoxidations, dehalogenations, and other reactions [4].
    
    [1] Takeda S, Usami N, Yamamoto I, et al. Cannabidiol-2′, 6′-dimethyl ether, a cannabidiol derivative, is a highly potent and selective 15-lipoxygenase inhibitor[J]. Drug Metabolism and Disposition, 2009, 37(8): 1733-1737.
    [2] Jiang R, Yamaori S, Okamoto Y, et al. Cannabidiol is a potent inhibitor of the catalytic activity of cytochrome P450 2C19[J]. Drug metabolism and pharmacokinetics, 2013, 28(4): 332-338.
    [3] Yamaori S, Maeda C, Yamamoto I, et al. Differential inhibition of human cytochrome P450 2A6 and 2B6 by major phytocannabinoids[J]. Forensic Toxicology, 2011, 29(2): 117-124.
    [4] Groves J T, Han Y Z. Models and mechanisms of cytochrome P450 action[M]//Cytochrome P450. Springer US, 1995: 3-48.
- Properties
  - Alternative Name
    
    CBDD,Cannabidiol-2',6'-dimethyl ether; 1,3-dimethoxy-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-benzene
    
    CAS Number
    
    1242-67-7
    
    Molecular Formula
    
    C23H34O2
    
    Molecular Weight
    
    342.5
    
    Appearance
    
    A solution in acetate. To change the solvent, simply evaporate the acetate containing under a gentle stream of nitrogen and immediately add the solvent of choice.
    
    Purity
    
    98.00%
    
    Solubility
    
    ≤14mg/ml in ethanol;1mg/ml in DMSO;2mg/ml in dimethyl formamide
    
    Storage
    
    Store at -20°C
    
    * For Research Use Only

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Cannabidiol dimethyl ether

Background

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